EP0907384B2 - Medical device - Google Patents

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Publication number
EP0907384B2
EP0907384B2 EP97930943A EP97930943A EP0907384B2 EP 0907384 B2 EP0907384 B2 EP 0907384B2 EP 97930943 A EP97930943 A EP 97930943A EP 97930943 A EP97930943 A EP 97930943A EP 0907384 B2 EP0907384 B2 EP 0907384B2
Authority
EP
European Patent Office
Prior art keywords
elongate shaft
isocyanate
solution
polyvinylpyrrolidone
curing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP97930943A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0907384B1 (en
EP0907384A1 (en
Inventor
Anette Israelsson
Jan Utas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Astra Tech AB
Original Assignee
Astra Tech AB
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Astra Tech AB filed Critical Astra Tech AB
Publication of EP0907384A1 publication Critical patent/EP0907384A1/en
Application granted granted Critical
Publication of EP0907384B1 publication Critical patent/EP0907384B1/en
Publication of EP0907384B2 publication Critical patent/EP0907384B2/en
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/04—Macromolecular materials
    • A61L29/041—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/04—Macromolecular materials
    • A61L29/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/056—Forming hydrophilic coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2387/00—Characterised by the use of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds

Definitions

  • the present invention relates to a method for producing a urinary catheter which present an elongate shaft having an outer surface coating for insertion into a passageway in a human or animal body.
  • catheters include those designated for urological, angioplasty and valvuloplasty uses, that is, adapted respectively for insertion into the urethra, the lumen of a blood vessel and heart passageway of a living body, normally a human body.
  • the material from which the elongate shaft is manufactured must fulfil such requirements as softness, good kink resistance, good dimensional stability, processability, for example ease to form and glue, and the possibility to be sterilised by radiation, steam, ethylene oxide or other means.
  • the material must accept a surface treatment which will impart desired surface properties to the medical device such as lubricity, hydrophilicity and blood compatibility.
  • the chemistry of the substrate material is critical since this affects the possibility to coat the substrate.
  • PVC polyvinyl chloride
  • prior European patent application publication No. 0093093 makes known a process for manufacturing a PVC urinary catheter having a hydrophilic outer surface coating which exhibits a low coefficient of friction when wetted.
  • the process involves forming a hydrophilic surface coating on the PVC catheter by sequentially applying a solution containing between 0.05-40% (weight/volume, that is, kg/l) of an isocyanate compound and a solution of polyvinylpyrrolidone (PVP) containing between 0.5-50% (weight/volume) to the outer surface of the catheter, for example by dipping, and then curing the hydrophilic coating at an elevated temperature advantageously in the presence of a water-containing gas such as ambient air.
  • PVP polyvinylpyrrolidone
  • the present invention provides a method for the manufacture of a urinary catheter which presents a hydrophilic surface coated elongate shaft for insertion into a body passageway comprising the steps of having the elongate shaft formed from a thermoplastic elastomer material selected from the group consisting of a polyether block amide and a styrene block copolymer and forming the hydrophilic coating on the elongate shaft by applying sequentially to the surface of the elongate shaft a solution comprising between 0.05 to 40% (weight to volume) of an isocyanate compound and a solution containing between 0.5 and 50% (weight to volume) of polyvinylpyrrolidone and curing at an elevated temperature wherein a hydrophilic polyvinypyrrolidone-polyurea interpolymer coating is formed, and wherein the curing is carried out in the presence of a water-containing gas.
  • a thermoplastic elastomer material selected from the group consisting of a polyether block amide and a s
  • the use of a polyether block amide or a styrene block copolymer results in an elongate shaft which undergoes substantially no shrinkage in the longitudinal direction as compared to PVC on application of the hydrophilic coating as well as providing an elongate shaft with the normal properties required for insertion thereof into a body passageway.
  • the present invention therefore enables a urinary catheter to be provided which addresses the aforementioned disadvantages of PVC based catheters leading to inter alia less wastage of starting materials and the possibility to use TV monitors for quality control.
  • the polyether block amide used in the invention is believed to have a structure as follows: wherein PA is a polyamide, PE is a polyether and n is an integer greater than 1 which represents the number of blocks of copolymer molecular repeating units within the molecular formula of the copolymer.
  • Representative polyether block amide materials include the Pebax® polymers (Elf Atochem S. A.).
  • the styrene block copolymer is a styrene-ethylene/butylene-styrene block copolymer, for example Evoprene® G (Evode Plastics Ltd.).
  • isocyanate solution to the elongate shaft surface results in a coating having unreacted isocyanate groups being formed on the elongate shaft surface.
  • Application of the polyvinylpyrrolidone solution to the elongate shaft surface then results in a hydrophilic polyvinylpyrrolidone-polyurea interpolymer coating being formed on the elongate shaft surface. Curing of this hydrophilic coating binds the isocyanate compounds together to form a stable non-reactive network that binds the hydrophilic polyvinylpyrrolidone. Curing takes place in the presence of a water-containing gas, for example ambient air, to enable the isocyanate groups to react with the water to yield an amine which rapidly reacts with other isocyanate groups to form a urea cross-link.
  • a water-containing gas for example ambient air
  • the method further comprises the steps of evaporating the solvent of the isocyanate solution prior to application of the polyvinylpyrrolidone solution and evaporating the solvent of the polyvinylpyrrolidone solution prior to curing of the hydrophilic coating. This may for example be done by air drying.
  • the isocyanate compound comprises at least two unreacted isocyanate groups per molecule.
  • the isocyanate may be selected from 2,4-toluene diisocyanate and 4,4'-diphenylmethane diisocyanate, or a pentamer of hexamethylene diisocyanate and toluene diisocyanate of cyanurate type, or trimerized hexamethylene diisocyanate biuret or mixtures thereof.
  • the solvent for the isocyanate compound is preferably one which does not react with isocyanate groups.
  • the preferred solvent is methylene chloride but it is also possible to use ethyl acetate, acetone, chloroform, methyl ethyl ketone and ethylene dichloride, for example.
  • the isocyanate solution may advantageously contain between 0.5 to 10% (weight to volume) of the isocyanate compound, and may preferably contain between 1 to 6% (weight to volume) of the isocyanate compound. Generally, the isocyanate solution only needs to be in contact with the surface briefly, for example 5 to 60 sec.
  • the elongate shaft may be swelled beforehand in a suitable solvent.
  • a solvent for the isocyanate solution which has the ability to swell or dissolve the elongate shaft surface which is to be coated.
  • catalysts for isocyanate curing may be added. These catalysts may be dissolved in either the isocyanate solution or the polyvinylpyrrolidone solution but are preferably dissolved in the latter.
  • Different types of amines are especially useful, for example diamines, but also for example triethylenediamine.
  • an aliphatic amine is employed which is volatisable at the drying and curing temperatures used for the coating, and which furthermore is non-toxic.
  • Suitable amines are N, N'diethylethylendiamine, hexamethylendiamine, ethylendiamine, paradiaminobenzene, 1,3-propandiol-para-aminobenzoic acid diester and diaminobicyclo-octane.
  • the proportion of catalyst in the solution is suitably between 0.1 to 50% by weight of the amount of polyvinylpyrrolidone, preferably between 0.1 to 10% by weight.
  • the polyvinylpyrrolidone used preferably has a mean molecular weight of between 10 4 to 10 7 with the most preferred mean molecular weight being about 10 5 .
  • Polyvinylpyrrolidone having such a molecular weight is commercially available, for example under the trademark Kollidon® (BASF).
  • suitable solvents for polyvinylpyrrolidone are methylene chloride (preferred), ethyl acetate, acetone, chloroform, methyl ethyl ketone and ethylene dichloride.
  • the proportion of polyvinylpyrrolidone in the solution is preferably between 0.5 to 10% (weight to volume) and most preferred between 2 to 8% (weight to volume).
  • the polyvinylpyrrolidone in the solvent is applied by dipping, spraying or the like for a short period of time, e.g. during 5 to 50 sec.
  • Curing of the coating is preferably performed at a temperature of 50 to 130° C, in for example an oven, for a duration of between 5 to 300 min.
  • the hydrophilic coating contains an osmolality-increasing compound, for instance an inorganic salt selected from sodium and potassium chlorides, iodides, citrates and benzoates.
  • an osmolality-increasing compound for instance an inorganic salt selected from sodium and potassium chlorides, iodides, citrates and benzoates.
  • the osmolality-increasing compound may be applied in the manner detailed in prior European patent application publication No. 0217771.
  • the polyether block amide or styrene block copolymer selected for the elongate shaft respectively has a hardness in the range 25 Sh D to 70 Sh D and 40 shore A to 70 shore D.
  • a urinary catheter preferably has a hardness in the range 25 Sh D to 45 Sh D for polyether block amide and 40 shore A to 45 shore D for styrene block copolymer.
  • a diisocyanate (named Desmodur IL) is dissolved in methylene chloride to a concentration of 2% (weight/volume).
  • a urinary catheter formed exclusively or essentially exclusively from Pebax® (hereinafter a "urinary Pebax® catheter") with a hardness of 70 shore D is dipped in this solution for 15 seconds and is then dried at ambient temperature for 60 seconds.
  • the catheter is then dipped for 1 second in a solution containing 6% (weight/volume) of polyvinylpyrrolidone (K90; mean molecular weight ⁇ 360 000) dissolved in methylene chloride.
  • K90 mean molecular weight ⁇ 360 000
  • the catheter is then allowed to dry at ambient temperature for 60 seconds and is finally cured for 50 minutes at 100 °C.
  • the catheter is finally allowed to cool to room temperature and is then rinsed in water.
  • the catheter has a slippery and adherent surface when wet.
  • a diisocyanate (named Desmodur IL) is dissolved in ethyl acetate to a concentration of 2% (weight/volume).
  • a urinary Pebax® catheter with a hardness of 35 shore D is dipped in this solution for 15 seconds and is then dried at ambient temperature for 60 seconds.
  • the catheter is then dipped for I second in a solution containing 6% (weight/volume) of polyvinylpyrrolidone (K90; mean molecular weight ⁇ 360 000) dissolved in ethyl lactate (50%) and ethyl acetate (50%).
  • K90 polyvinylpyrrolidone
  • ethyl lactate 50%
  • the catheter is then allowed to dry at ambient temperature for 60 seconds and is finally cured for 50 minutes at 80 °C.
  • the catheter is finally allowed to cool to room temperature and is then rinsed in water.
  • the catheter has a slippery and adherent surface when wet.
  • a diisocyanate (named Desmodur IL) is dissolved in methylene chloride (75%) and tri chloro ethylene (25%) to a concentration of 2% (weight/volume).
  • a urinary Pebax® catheter with a hardness of 63 shore D is dipped in this solution for 15 seconds and is then dried at ambient temperature for 60 seconds.
  • the catheter is then dipped for 1 second in a solution containing 6% (weight/volume) of polyvinylpyrrolidone (K90; mean molecular weight ⁇ 360 000) dissolved in methylene chloride (75%) and tri chloro ethylene (25%).
  • K90 polyvinylpyrrolidone
  • the catheter is then allowed to dry at ambient temperature for 60 seconds and is finally cured for 50 minutes at 100 °C.
  • the catheter is finally allowed to cool to room temperature and is then rinsed in water.
  • the catheter has a slippery and adherent surface when wet.
  • a diisocyanate (named Desmodur IL) is dissolved in ethyl acetate to a concentration of 2% (weight/volume).
  • a urinary catheter manufactured from Evoprene® G with a hardness of 65 shore A is dipped in this solution for 15 seconds and is then dried at ambient temperature for 60 seconds.
  • the catheter is then dipped for 1 second in a solution containing 6% (weight/volume) of polyvinylpyrrolidone (K90; mean molecular weight ⁇ 360 000) dissolved in methylene chloride.
  • K90 mean molecular weight ⁇ 360 000
  • the catheter is then allowed to dry at ambient temperature for 60 seconds and is finally cured for 50 minutes at 100 °C.
  • the catheter is finally allowed to cool to room temperature and is then rinsed in water.
  • the catheter has a slippery and adherent surface when wet.
  • the urinary catheters prepared according to the examples show low friction, good kink resistance, good dimension stability and possibility to be sterilised. Moreover, the longitudinal shrinkage of the catheters as a result of the coating process was less than 1% of the original length.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Materials For Medical Uses (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP97930943A 1996-06-26 1997-06-19 Medical device Expired - Lifetime EP0907384B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SE9602529A SE9602529D0 (sv) 1996-06-26 1996-06-26 Medical device
SE9602529 1996-06-26
PCT/SE1997/001121 WO1997049437A1 (en) 1996-06-26 1997-06-19 Medical device

Publications (3)

Publication Number Publication Date
EP0907384A1 EP0907384A1 (en) 1999-04-14
EP0907384B1 EP0907384B1 (en) 2003-02-26
EP0907384B2 true EP0907384B2 (en) 2007-06-13

Family

ID=20403170

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97930943A Expired - Lifetime EP0907384B2 (en) 1996-06-26 1997-06-19 Medical device

Country Status (28)

Country Link
US (1) US6629961B1 (pt)
EP (1) EP0907384B2 (pt)
JP (1) JP4331796B2 (pt)
AR (1) AR007630A1 (pt)
AT (1) ATE233109T1 (pt)
BE (1) BE1012747A3 (pt)
BR (1) BR9709885A (pt)
CZ (1) CZ296626B6 (pt)
DE (1) DE69719328T3 (pt)
DK (1) DK0907384T4 (pt)
ES (1) ES2193384T5 (pt)
FR (1) FR2750337B1 (pt)
HU (1) HU224142B1 (pt)
ID (1) ID20531A (pt)
IE (1) IE970466A1 (pt)
IL (1) IL127735A (pt)
IS (1) IS4921A (pt)
IT (1) IT1292206B1 (pt)
NL (1) NL1006411C2 (pt)
NO (1) NO318558B1 (pt)
NZ (1) NZ333225A (pt)
PL (1) PL189111B1 (pt)
PT (1) PT907384E (pt)
RU (1) RU2213582C2 (pt)
SE (1) SE9602529D0 (pt)
TR (1) TR199802681T2 (pt)
WO (1) WO1997049437A1 (pt)
ZA (1) ZA975593B (pt)

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EP1745807B1 (en) 2005-07-18 2012-08-22 Dentsply IH AB Urinary catheter
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US7906066B2 (en) * 2006-06-30 2011-03-15 Abbott Cardiovascular Systems, Inc. Method of making a balloon catheter shaft having high strength and flexibility
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US8403885B2 (en) 2007-12-17 2013-03-26 Abbott Cardiovascular Systems Inc. Catheter having transitioning shaft segments
CN101965372A (zh) 2008-01-04 2011-02-02 Cr巴德公司 合成聚异戊二烯福利导管
US20090208368A1 (en) * 2008-02-14 2009-08-20 Kent Waldrep Urinary catheter, catheter packaging assembly and method of use
JP2011526814A (ja) 2008-06-30 2011-10-20 シー．アール．バード，インコーポレイテッド ポリウレタン／ポリイソプレンブレンドカテーテル
US8444608B2 (en) 2008-11-26 2013-05-21 Abbott Cardivascular Systems, Inc. Robust catheter tubing
US8052638B2 (en) 2008-11-26 2011-11-08 Abbott Cardiovascular Systems, Inc. Robust multi-layer balloon
CA2752035A1 (en) 2009-02-20 2010-08-26 Boston Scientific Scimed, Inc. Hydrophilic coating that reduces particle development on ester-linked poly(ester-block-amide)
WO2011063816A1 (en) * 2009-11-26 2011-06-03 Coloplast A/S A telescopic device
US8287890B2 (en) * 2009-12-15 2012-10-16 C.R. Bard, Inc. Hydrophilic coating
FR2962043B1 (fr) * 2010-07-01 2013-02-01 Arkema France Composition cosmetique comprenant du peba
CN107007921B (zh) 2011-05-26 2020-01-21 雅培心血管系统有限公司 导管的贯通顶端
CA2861314C (en) * 2012-01-18 2021-03-16 Surmodics, Inc. Lubricious medical device coating with low particulates
US8684963B2 (en) 2012-07-05 2014-04-01 Abbott Cardiovascular Systems Inc. Catheter with a dual lumen monolithic shaft
HUE050800T2 (hu) 2014-12-29 2021-01-28 Dentsply Ih Ab Húgyúti katéter puha heggyel
WO2019089875A1 (en) 2017-11-03 2019-05-09 Hollister Incorporated Methods of bonding components to polymeric substrates
LT4176908T (lt) 2018-05-17 2024-08-26 Hollister Incorporated Būdai gaminti hidrofilinių kateterių su rankovėmis rinkinius
WO2021257445A1 (en) * 2020-06-18 2021-12-23 Saint-Gobain Performance Plastics Corporation Hydrophilic thermal plastic elastomer
EP4049689A1 (en) 2021-02-25 2022-08-31 Dentsply IH AB Medical device with substrate comprising natural fibers

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Also Published As

Publication number Publication date
ITMI971512A0 (pt) 1997-06-26
BR9709885A (pt) 1999-08-10
PT907384E (pt) 2003-07-31
CZ427198A3 (cs) 1999-03-17
NO318558B1 (no) 2005-04-11
ES2193384T5 (es) 2007-12-01
FR2750337B1 (fr) 2001-07-13
RU2213582C2 (ru) 2003-10-10
IL127735A (en) 2004-06-01
HUP9902969A2 (hu) 2000-01-28
DE69719328T2 (de) 2003-12-11
DE69719328T3 (de) 2007-12-27
WO1997049437A1 (en) 1997-12-31
IE970466A1 (en) 2000-08-23
IL127735A0 (en) 1999-10-28
HUP9902969A3 (en) 2000-02-28
AU3469997A (en) 1998-01-14
JP2000513959A (ja) 2000-10-24
PL330714A1 (en) 1999-05-24
ITMI971512A1 (it) 1998-12-26
EP0907384B1 (en) 2003-02-26
AR007630A1 (es) 1999-11-10
BE1012747A3 (fr) 2001-03-06
EP0907384A1 (en) 1999-04-14
ATE233109T1 (de) 2003-03-15
AU710718B2 (en) 1999-09-30
NO986048L (no) 1999-02-26
NO986048D0 (no) 1998-12-22
DK0907384T3 (da) 2003-06-16
NZ333225A (en) 1999-05-28
TR199802681T2 (xx) 1999-03-22
ES2193384T3 (es) 2003-11-01
ID20531A (id) 1999-01-07
DK0907384T4 (da) 2007-10-08
SE9602529D0 (sv) 1996-06-26
PL189111B1 (pl) 2005-06-30
US6629961B1 (en) 2003-10-07
IS4921A (is) 1998-12-11
JP4331796B2 (ja) 2009-09-16
HU224142B1 (hu) 2005-05-30
ZA975593B (en) 1997-12-26
CZ296626B6 (cs) 2006-05-17
NL1006411A1 (nl) 1998-01-07
IT1292206B1 (it) 1999-01-25
FR2750337A1 (fr) 1998-01-02
DE69719328D1 (de) 2003-04-03
NL1006411C2 (nl) 2000-08-08

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